Luke Bryan Opens Up About His Family's Heartbreaking Tragedies

At age 19, Luke Bryan was getting ready to move to Nashville (he even had an apartment lined up) when his older brother, Chris Bryan, was killed in a car accident. The devastating loss threw him for a loop, but also served as a stark reminder about life's fragile nature. Bryan delayed the move—finishing his education at Georgia Southern University and meeting the woman he'd one day marry in the meantime—but after four years, his dad insisted he pursue Music City, telling him, "This life will always be there."

The life Bryan's father referred to was his country roots: The singer-songwriter grew up on a farm in rural Leesburg, Georgia, the youngest of three children including a sister, Kelly. "He was really adamant about me chasing my dreams," Bryan told ABC's Robin Roberts during a special Living Every Day: Luke Bryan that aired Nov. 6.

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Bryan found Nashville "liberating" and it wasn't long before he was writing songs for artists like Travis Tritt, including the title track of Tritt's 2004 album My Honky Tonk History. He signed with Capitol Nashville in 2004 and released his first hit single, "All My Friends Say," three years later.

He married his college sweetheart, Caroline Boyer, in December 2006 (the couple will celebrate their 11th anniversary next month). "When I moved to Nashville and started my family I was really determined to create a situation where they would grow up with a country style of life," Bryan told Roberts, adding that he wanted his children to learn how to hunt and fish.

Then, in May 2007, tragedy struck again. Bryan's sister, Kelly, died unexpectedly while at home with her young son. "They never determined what happened. The autopsies, the coroner, no one could figure it out," Bryan toldPeople in 2013. He had just seen her one month before when she'd come to watch his Grand Ole Opry performance. The photo they took that night was their last one together.

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His son Bo was born nearly a year later, followed by a second son, Tate, in 2010. Caroline describes Bo as more like his father (he "wakes up singing and dancing"), while Tate "likes to be in the background and that is exactly how I am; I don't want to be front and center," she told Roberts from the family's Red Bird Farm in Tennessee, named so because both she and Bryan's sister had a habit of wishing upon crimson-colored fliers.

When Kelly's husband, Ben Lee Cheshire, who'd been raising their children alone after her death, died in 2014, Luke and Caroline became the parents of three more: Jordan, 22, Kris, 19, and Til, 15.

"We never thought twice about it," said Caroline about taking in their two nieces and nephew. "You know, it was never something that he and I had to sit down and talk about, you know, should we take this on? We just did it."

"I've watched my family go through ebbs and flows where we get mad at God and we get mad at why this has happened," said Bryan. "Well, you keep going and you try to, try to be as positive as you can, and you try to appreciate every day ... You'll never get back to 100 percent. You'll always be working to get back to 75 percent."

Earlier this year, they experienced a loss on Caroline's side of the family, too: her niece, Sadie Brett, passed away at just seven months old. They've honored her with a structure emblazoned with the moniker "Brett's Barn" and a field of bright flowers on the farm.

"You have to honor their memory by living, you have to be a positive light for people," said Bryan. "If you live long enough life's going to get you a little bit."

But not all tears are sad ones for the Bryan family, though. When Bryan won CMA Entertainer of the Year for the first time in 2014 (he also won in 2015 and is nominated again this year) the group got "together and celebrated and cried," he said. "It certainly makes it special when we're all together and we know that people are smiling down, and they're, they're with us, celebrating these amazing moments."

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